What is the Difference Between Sulfone and Sulfoxide?

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Sulfone and sulfoxide are organic compounds containing sulfur atoms. The key difference between them is the number of double-bonded oxygen atoms in their respective functional groups:

  • Sulfone: Contains a sulfonyl functional group (R−S(=O)2−R’) with two double-bonded oxygen atoms and a central hexavalent sulfur atom. Sulfones are typically prepared by organic oxidation of thioethers, often referred to as sulfides. They are relatively inert functional groups, being weakly basic compared to sulfoxides.
  • Sulfoxide: Contains a sulfoxide functional group with only one double-bonded oxygen atom. Sulfoxides are intermediates in the synthesis of sulfones from thioethers. They have a lone pair of electrons on the sulfur atom, making the sulfoxide group nonplanar. Most sulfoxides are colorless liquids or solids with low melting points.

In summary, sulfones have two double-bonded oxygen atoms in their sulfonyl functional group, while sulfoxides have only one double-bonded oxygen atom in their functional group.

Comparative Table: Sulfone vs Sulfoxide

Here is a table comparing the differences between sulfone and sulfoxide:

Property Sulfone Sulfoxide
Definition Sulfone is an organic compound containing a sulfonyl functional group attached to two carbon atoms, with a central sulfur atom having two double-bonded oxygen atoms. Sulfoxide is an organic compound containing a central sulfur atom attached to two carbon atoms, with one double-bonded oxygen atom and one single-bonded oxygen atom.
Sulfur Atom Oxidation State +6. +6.
S=O Bonds Two double-bonded S=O bonds. One double-bonded and one single-bonded S=O bond.
Acidity Sulfones tend to be more acidic than sulfoxides. Sulfoxides are less acidic than sulfones.
Reactions Sulfones can be obtained by oxidizing sulfoxides. Sulfoxides can be obtained by oxidizing sulfides.

Both sulfone and sulfoxide are organic compounds containing a central sulfur atom. However, the key difference between them is the number of double-bonded oxygen atoms attached to the sulfur atom: sulfones have two double-bonded oxygen atoms, while sulfoxides have only one.